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By Europe specialist Jeff

Timeworn ancient temples or soaring Renaissance domes? Multitudes of alluring islands or dramatic coastal pathways? The heart of olive oil or the home of pasta? A trip combining Greece and Italy is one that I love to recommend to visitors with three weeks or more to explore.

Why combine Greece & Italy?

For many, choosing which country to visit in Europe is often the hardest decision, so I suggest starting with a combination trip to Greece and Italy, taken at a relaxed pace. While they’re not directly linked along the border, it’s easy to hop between the two via a direct flight of under two hours. A combination trip offers you the chance to explore the art cities, ancient sites, eclectic islands, and diverse cultures together in one trip.

Below are a few of my top Greece and Italy holiday ideas, but we can link the two countries together in a multitude of ways that reflect your own personal interests.

1. Historic Greece and the Amalfi coast in Italy

Mainland Greece is an absolute haven for historical explorers, with a plethora of sites to visit. Following a trip here with the serenity of the Italian coast near Naples gives you a good counterbalance to a busy adventure.

In Athens, we can arrange a multitude of privately guided trips, from tours of the key sites to get your bearings, to more in-depth time at the Parthenon, the Acropolis Museum, or the Ancient Agora marketplace. From Athens, it’s a two-and-a-half-hour drive up to Delphi, where your private guide can walk you through this spectacular archaeological site, perched on the slopes of Mount Parnassus. You’ll head to Nafplio next, the first capital of modern Greece and one of the most beautiful coastal towns in the eastern Peloponnese, with its mix of Venetian and Turkish architecture. Maybe breaking up the journey with a visit to Skouras winery in the Nemea wine region, for lunch and wine tasting.

From Nafplio, we can arrange private tours of the remains at Mycenae and the so-called Tomb of Agamemnon, or kayaking adventures to the sunken ruins at Epidavros, before returning to Athens to board your onward flight to Italy.

Arriving in Naples, you’ll have a short drive of 1.5 hours, skirting the Bay of Naples and heading along the peninsular to Sorrento. This is the ideal gateway for exploring the Amalfi Coast, renowned for its beautiful, rocky coastline, lemon trees, and translucent waters.

You might wish to accompany one of our private guides and discover the cliffside village of Positano, explore the island of Ischia — where you can take advantage of its abundant hot springs, or climb Mount Vesuvius. If you’re excited to add one last historic slant, a privately guided visit to the remains of Pompeii or Herculaneum makes a fascinating end to the trip.

2. Outdoor adventures in Greece and Italy

Combining Greece and Italy is an ideal choice for those seeking a trip that includes plenty of alfresco activities. I would suggest starting first in Greece, flying directly to Athens, where you could easily stay for a couple of nights to ensure that you see the main sights of the city. From here, we can arrange for a private driver to take you north, where the adventures begin.

You’ll have a stop to walk the impressive remains at Delphi on route up to the monasteries of Meteora. Here, where we can arrange a half day e-bike tour of the area, with a private guide giving you an insight into the history of the cliff-top monasteries as you cycle between, and pop in to visit, the six monasteries that remain in use today. Your tour includes time at a panoramic viewpoint to watch the sun dip behind the monasteries, enveloping them in its evening glow.

From here, the adventures are endless, from a 4x4 safari around the Pindus Mountains, to a guided group hike through Enipeas Gorge at the base of Mount Olympus, or exploring Thessaloniki — birthplace of Alexander the Great — with a private walking tour to immerse yourself in the history here that dates back to the 4th century.

From Thessaloniki, you’ll fly to Venice for a transfer to the Dolomites, one of the best places for activity holidays in Italy, and home to some indulgent boutique spa hotels around Madonna di Campiglio — perfect to recuperate in afterwards.

You may wish to head out with a guide to hike along the trails of Adamello-Brenta Nature Park, the mountain paths span 450km (280 miles) here, and take you through fir woods, larch forests, and past turquoise lakes, or you may prefer mountain biking the popular tracks in Val Rendena, a scenic valley crisscrossed with 30km (19 miles) of bike trails.

3. Food and wine of Greece and Italy

You’ll start your adventure in Greece, flying into the gastronomic capital of Athens. You might want to walk the narrow, cobblestoned streets of Plaka with its multitude of streetside tavernas, cafes, and restaurants, or head out on a private food tour, enjoying tasting experiences across the city and giving you a rich insight into the gourmet culture.

You can join a regional cooking class here, or make a connection when you share traditional food in the home of a local Athenian. To sample the local wine, we can easily incorporate a drive out into the Nemea wine region, where a private guide can take you on tours and tastings at a leading winery.

You’ll board a flight to Florence next, landing in the centre of Tuscan food and wine, and you can immerse yourself in both. From cellar tours and tastings in leading wineries, to truffle hunting in the Tuscan hills, or speciality cooking classes in everything from pasta making to tiramisu.

On to Rome, where you’ll join a small group food tour of the city, exploring the Jewish Ghetto and the vibrant Campo de’Fiori, with plenty of stops for sampling and to talk to local vendors. You may want to whiz around the city on the back of a Vespa, take time with a guide to see all the ancient sights, or finish your stay with a pizza-making class.

Finally, you’ll head further south to Naples, where you can be led by a private guide on a street-food and art tour of this lively, cosmopolitan city. To relax at the end of your trip, you can drive along the Amalfi Coast, stopping at a winery to sample the produce of these steep hillside vineyards, before heading out on a sunset cruise along the Sorrentine Coast.

4. Greek and Italian island hopping

Both Italy and Greece boast some of the most enticing islands in the Mediterranean and you can easily combine adventures across both.

I like to suggest starting your trip in Sicily, which is a tapestry of cultural influence, with Hellenic roots in the southeast corner of the island. You’ll start your trip in Palermo, with a private walking tour of the city, taking in the eclectic mix of Byzantine and Baroque architecture.

From Palermo, you’ll head down to Agrigento for a private tour of the Temple of Jupiter and the Valley of the Temples, before heading on to the glamorous town of Taormina. While here, you may wish to include a guided hike up to the volcanic heights of Mount Etna. Potentially following this with a wine-tasting lunch, sampling wine produced from grapes grown in the rich volcanic soils.

From Sicily, you can take a flight to Corfu. A mix of Italian and Greek influences pervades this island, so it's a perfect mid-point to include on a trip blending both countries. You can dip into the cultural heritage of Corfu Old Town with a private food and history walking tour, or explore the island’s famed green hills with a guided hike along the remote trails that wind along the coastline.

If time allows, you may wish to complete your island hopping with one other group of Greek islands in Greece. I would highly recommend flying on to Athens from Corfu, before taking a ferry out to the Cycladic islands, in particular Milos, Naxos and Paros — you can easily move between the three via the ferry network. Here, you can indulge in island life to the full, with private catamaran cruises, 4x4 tours of the volcanic interiors, and stays in distinctive, whitewashed villages.

5. Romantic trip to Greece and Italy

From captivating views across the Amalfi Coast to sunsets reflected across the mirror-like waters of the Aegean Sea, combining the wonders of Greece and Italy will bring many memory-making moments. You can start in in Rome with intimate introductions to this romantic city. You might choose private guided tours of the Vatican, including Michelangelo’s Sistine Chapel ceiling and St Peter’s Basilica, or opt for walking food tours around the quieter areas of the city to sample highlights of Roman food, wine, and coffee.

From here you’ll head to Praiano on the Amalfi Coast, where you can hike with a guide overlooking the panoramic views of the coastline on the Path of the Gods. Or, you might wish to enjoy the fabulous restaurants and wine tasting tours that we can organise in this area.

You’ll fly directly from Naples to Santorini, a volcanic island known for its whitewashed villages that perch atop vertiginous, red cliffs overlooking the Aegean Sea. Here, you’ll stay in Chromata Hotel — a boutique property that makes the most of its panoramic coastal views.

Santorini’s volcanic soil is a fertile haven for wine growers and, as a result, it's one of the most important wine regions in Greece. You’ll be taken by a private driver to learn about wine production here and sample wines at two of the leading wineries. We can get you onto the crystalline waters too, heading out on a catamaran to explore the flooded caldera, with time to swim before sitting back and enjoying the sunset.

Leaving Santorini, you’ll board a ferry for Mykonos, from where you can explore the remote, archaeological treasure island of Delos with a private guide and enjoy some coastal downtime before the flight home.

6. Art of Italy and Greece

Italy is ablaze with artistic and architectural masterpieces, nowhere more so than in the ultimate triumvirate of Venice, Florence and Rome. You can begin a combined holiday to Italy and Greece by private tours in each of these three cities, hopping between them easily by train.

Alongside city walking tours with a private guide, we can arrange for you to be taken to secret chambers within the Venetian Doge’s Palace, on introductions to the art in Florence’s Pitti Palace and Uffizi Gallery, deep within the Colosseum in Rome, and beneath Michelangelo’s ceiling in the Sistine Chapel.

After this immersion in Italian art, you’ll fly from Rome to Crete, where you’ll have the opportunity to soak into the beauty of the southern Mediterranean. Crete has some indulgent hotels, particularly on its eastern side in Agios Nikolaos. You may choose to stay at the Minos Beach Art Hotel, which is right on the waterfront and makes the most of its setting with paddle board and motorboat rental.

You can also head over by private boat from here to the fascinating island of Spinalonga, featured in Victoria Hislop’s book, The Island. If you’re looking to delve into the cultural heritage of Crete, we can arrange for you to have a private tour of the Palace of Knossos, thought to have inspired the legend of the Minotaur, or you can climb with a guide high into the mountains above Lasithi to the caves where, according to Greek mythology, Zeus was born.

End your trip with a few nights in Athens before you head home. In keeping with the artistic theme of this combination, you might take a half-day, privately guided, street art tour.

Best time to visit Greece & Italy

Greece and Italy are both hot and busy in the peak summer months, so we recommend visiting either side of these, during the spring (April to June) and early autumn (September and October). During these months you’ll find the temperature warm, the landscape vibrant, and all the main sights open but quieter — ideal for exploring.